AR042658A1 - DERIVATIVES OF 1,5-DIARIL-PIRROL-3-CARBOXAMIDE AND ITS USE AS CANABINOID RECEIVER MODULATORS - Google Patents

DERIVATIVES OF 1,5-DIARIL-PIRROL-3-CARBOXAMIDE AND ITS USE AS CANABINOID RECEIVER MODULATORS

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Publication number
AR042658A1
AR042658A1 ARP030104797A ARP030104797A AR042658A1 AR 042658 A1 AR042658 A1 AR 042658A1 AR P030104797 A ARP030104797 A AR P030104797A AR P030104797 A ARP030104797 A AR P030104797A AR 042658 A1 AR042658 A1 AR 042658A1
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Argentina
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group
alkyl
optionally substituted
alkyl group
groups
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ARP030104797A
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Spanish (es)
Inventor
Anna Ingrid Kristina Berggren
Stig Jonas Bostrom
Leifeng Cheng
Stig Thomas Elebring
Peter Greasley
Mats Nagard
Johan Michael Wilstermann
Emma Terricabras
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Astrazeneca Ab
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Publication of AR042658A1 publication Critical patent/AR042658A1/en

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    • A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
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    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Abstract

Un compuesto de fórmula (1), procesos para preparar tales compuestos, su uso en el tratamiento de obesidad, trastornos psiquiátricos y neurológicos, particularmente obesidad, métodos para su uso terapéutico y composiciones farmacéuticas que los contienen. Reivindicación 1: Un compuesto caracterizado porque responde a la fórmula (1), y sales, profármacos y solvatos aceptables para uso farmacéutico del mismo, en donde R1 y R2 representan en forma independiente fenilo, tienilo o piridilo cada uno de los cuales está opcionalmente sustituido por uno, dos o tres grupos representados por Z; Z representa un grupo alquilo C1-3, un grupo alcoxi C1-3, hidroxi, halo, trifluorometilo, trifluorometiltio, difluorometoxi, trifluorometoxi, trifluorometilsulfonilo, amino, mono o di-alquilamino (C1-3), mono o di-alquilamido (C1-3), alquilsulfonilo C1-3, alcoxicarbonilo C1-3, carboxi, ciano, carbamoílo, mono o di-alquilo (C1-3) carbamoílo, sulfamoilo y acetilo; y R3 es H, un grupo alquilo C1-3, un grupo alcoximetilo C1-3, trifluorometilo, un grupo amino-alquilo (C1-3), un grupo hidroxi-alquilo (C1-3), alcoxicarbonilo C1-3, carboxi, ciano, carbamoílo, mono o di-alquilcrbamoilo (C1-3), acetilo, o hidrazinocarbonilo de fórmula -CONHNRaRb donde Ra y Rb son como se define para R4 y R5 respectivamente y; X es CO o SO2; Y está ausente o representa NH opcionalmente sustituido con un grupo alquilo C1-3; R4 y R5 representan en forma independiente un grupo alquilo C1-6; un grupo (amino)alquilo C1-4 en donde el amino está opcionalmente sustituido con uno o más grupos alquilo C1-3; un grupo carbocíclico C3-15 no aromático opcionalmente sustituido; un grupo cicloalquil(C3-12)-alquilo(C1-3); un grupo -(CH2)r(fenil)s en donde r es 0, 1, 2, 3 ó 4, s es 1 cuando r es 0, caso contrario, s es 1 ó 2 y los grupos fenilo están sustituidos opcionalmente en forma independiente por uno, dos o tres grupos representados por Z; naftilo; antracenilo; un grupo heterocíclico saturado de 5 a 8 miembros que contiene un nitrógeno y opcionalmente uno de los siguientes: oxígeno, azufre o un nitrógeno adicional donde el grupo heterocíclico está opcionalmente sustituido con uno o más grupos alquilo C1-3, hidroxi o bencilo; 1-adamantilmetilo; un grupo -(CH2)thet en donde t es 0, 1, 2, 3 ó 4, y la cadena alquileno está opcionalmente sustituida por uno o más grupos alquilo C1-3 y Het representa un heterociclo aromático opcionalmente sustituido por uno, dos o tres grupos seleccionados entre un grupo alquilo C1-6; un grupo alcoxi C1-6 o halo; o R4 representa H y R5 tiene los valores que se han definido; o R4 y R5 junto con el átomo de nitrógeno al cual están unidos representan un grupo heterocíclico saturado de 5 a 8 miembros que contiene un nitrógeno y opcionalmente uno de los siguientes: oxígeno, azufre o un nitrógeno adicional; donde el grupo heterocíclico está opcionalmente sustituido con uno o más grupos alquilo C1-3, hidroxi o bencilo; R6 es H, un grupo alquilo C1-3, un grupo alcoximetilo C1-3, trifluorometilo, un grupo hidroxi-alquilo (C1-3), alcoxicarbonilo C1-3, carboxi, ciano, carbamoílo, mono o di-alquilcarbamoilo (C1-3), acetilo, o hidrazinocarbonilo de fórmula -CONHRaRb donde Ra y Rb son como se define para R4 y R5 respectivamente y; con la salvedad de que cuando R6 es metilo entonces el grupo X-Y-NR4R5 no representa CONHC6H13, CONHC12H25, CONH2, CONHCH3, CON(CH3)2, o un resto de fórmula (2), y con la salvedad adicional de que cuando R1 y R2 representan en forma independiente fenilo entonces Z no es un grupo ortometilo.A compound of formula (1), processes for preparing such compounds, their use in the treatment of obesity, psychiatric and neurological disorders, particularly obesity, methods for therapeutic use and pharmaceutical compositions containing them. Claim 1: A compound characterized in that it responds to formula (1), and salts, prodrugs and solvates acceptable for pharmaceutical use thereof, wherein R1 and R2 independently represent phenyl, thienyl or pyridyl each of which is optionally substituted. by one, two or three groups represented by Z; Z represents a C1-3 alkyl group, a C1-3 alkoxy group, hydroxy, halo, trifluoromethyl, trifluoromethylthio, difluoromethoxy, trifluoromethoxy, trifluoromethylsulfonyl, amino, mono or di-alkylamino (C1-3), mono or di-alkylamido (C1 -3), C1-3 alkylsulfonyl, C1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di (C1-3) alkyl carbamoyl, sulfamoyl and acetyl; and R3 is H, a C1-3 alkyl group, a C1-3 alkoxymethyl group, trifluoromethyl, an amino (C1-3) alkyl group, a hydroxy (C1-3) alkyl group, C1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di-C 1-3 alkyl, acetyl, or hydrazinocarbonyl of the formula -CONHNRaRb where Ra and Rb are as defined for R4 and R5 respectively and; X is CO or SO2; Y is absent or represents NH optionally substituted with a C1-3 alkyl group; R4 and R5 independently represent a C1-6 alkyl group; a C1-4 (amino) alkyl group wherein the amino is optionally substituted with one or more C1-3 alkyl groups; an optionally substituted C3-15 non-aromatic carbocyclic group; a (C3-12) cycloalkyl (C1-3) alkyl group; a group - (CH2) r (phenyl) s where r is 0, 1, 2, 3 or 4, s is 1 when r is 0, otherwise, s is 1 or 2 and the phenyl groups are optionally substituted in form independent by one, two or three groups represented by Z; naphthyl; anthracenyl; a saturated 5- to 8-membered heterocyclic group containing a nitrogen and optionally one of the following: oxygen, sulfur or an additional nitrogen where the heterocyclic group is optionally substituted with one or more C1-3 alkyl, hydroxy or benzyl groups; 1-adamantylmethyl; a group - (CH2) thet wherein t is 0, 1, 2, 3 or 4, and the alkylene chain is optionally substituted by one or more C1-3 alkyl groups and Het represents an aromatic heterocycle optionally substituted by one, two or three groups selected from a C1-6 alkyl group; a C1-6 alkoxy or halo group; or R4 represents H and R5 has the values that have been defined; or R4 and R5 together with the nitrogen atom to which they are attached represent a saturated 5- to 8-membered heterocyclic group containing a nitrogen and optionally one of the following: oxygen, sulfur or an additional nitrogen; wherein the heterocyclic group is optionally substituted with one or more C1-3 alkyl, hydroxy or benzyl groups; R6 is H, a C1-3 alkyl group, a C1-3 alkoxymethyl group, trifluoromethyl, a hydroxy (C1-3) alkyl, C1-3 alkoxycarbonyl, carboxy, cyano, carbamoyl, mono or di-alkylcarbamoyl (C1- 3), acetyl, or hydrazinocarbonyl of the formula -CONHRaRb where Ra and Rb are as defined for R4 and R5 respectively and; with the proviso that when R6 is methyl then the group XY-NR4R5 does not represent CONHC6H13, CONHC12H25, CONH2, CONHCH3, CON (CH3) 2, or a remainder of formula (2), and with the additional proviso that when R1 and R2 independently represent phenyl so Z is not an orthomethyl group.

ARP030104797A 2002-12-24 2003-12-22 DERIVATIVES OF 1,5-DIARIL-PIRROL-3-CARBOXAMIDE AND ITS USE AS CANABINOID RECEIVER MODULATORS AR042658A1 (en)

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US (1) US20060122230A1 (en)
EP (1) EP1578417A1 (en)
JP (1) JP2006513201A (en)
KR (1) KR20050086931A (en)
CN (1) CN1753668A (en)
AR (1) AR042658A1 (en)
AU (1) AU2003290292A1 (en)
BR (1) BR0317705A (en)
CA (1) CA2511601A1 (en)
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Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0403780D0 (en) * 2004-02-20 2004-03-24 Astrazeneca Ab Therapeutic agents
CN101006052B (en) * 2004-07-30 2013-11-06 埃克塞利希斯股份有限公司 Pyrrole derivatives as pharmaceutical agents
BRPI0513677B8 (en) * 2004-07-30 2021-05-25 Exelixis Inc pyrrole derivatives as pharmaceutical agents
FR2874012B1 (en) * 2004-08-09 2008-08-22 Sanofi Synthelabo PYRROLE DERIVATIVES, THEIR PREPARATION AND USE IN THERAPEUTICS
FR2882054B1 (en) * 2005-02-17 2007-04-13 Sanofi Aventis Sa 1,5-DIARYLPYRROLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
FR2887548B1 (en) * 2005-06-27 2007-09-21 Sanofi Aventis Sa 4,5-DIARYLPYRROLE DERIVATIVES, THEIR PREPARATION AND THERAPEUTIC USE THEREOF
PE20070182A1 (en) 2005-07-29 2007-03-06 Wyeth Corp CYANOPYRROL-PHENYL AMIDE DERIVATIVES AS PROGESTERONE RECEPTOR MODULATORS
WO2007020502A2 (en) * 2005-08-16 2007-02-22 Pharmacia & Upjohn Company Llc Cannabinoid receptor ligands and uses thereof
AU2006294579A1 (en) 2005-09-27 2007-04-05 Myriad Genetics, Inc. Pyrrole derivatives as therapeutic compounds
CA2642619A1 (en) * 2006-02-20 2007-08-30 Astellas Pharma Inc. Pyrrole derivative or salt thereof
EP2061767B1 (en) 2006-08-08 2014-12-17 Sanofi Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use
EP2059238A4 (en) * 2006-09-07 2011-04-06 Myriad Genetics Inc Therapeutic compounds for diseases and disorders
TW200831080A (en) * 2006-12-15 2008-08-01 Irm Llc Compounds and compositions as inhibitors of cannabinoid receptor 1 activity
TW200848019A (en) 2007-03-06 2008-12-16 Wyeth Corp Aryl sulfonamides useful for modulation of the progesterone receptor
EP2025674A1 (en) 2007-08-15 2009-02-18 sanofi-aventis Substituted tetra hydro naphthalines, method for their manufacture and their use as drugs
SI2963031T1 (en) 2007-11-30 2019-04-30 Zynerba Pharmaceuticals, Inc. Prodrugs of tetrahydrocannabinol, compositions comprising prodrugs of tetrahydrocannabinol and methods of using the same
US8426448B2 (en) * 2008-04-22 2013-04-23 Eli Lilly And Company 1,5-diphenyl-pyrrolidin-2-one compounds as CB-1 ligands
FR2930939B1 (en) * 2008-05-09 2010-07-30 Sanofi Aventis PYRROLE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
TW201014822A (en) 2008-07-09 2010-04-16 Sanofi Aventis Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof
WO2010068601A1 (en) 2008-12-08 2010-06-17 Sanofi-Aventis A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof
DK2470552T3 (en) 2009-08-26 2014-02-17 Sanofi Sa NOVEL, CRYSTALLINE, heteroaromatic FLUORGLYCOSIDHYDRATER, MEDICINES COVERING THESE COMPOUNDS AND THEIR USE
US20130109721A1 (en) * 2009-12-08 2013-05-02 Ironwood Pharmaceuticals, Inc. FAAH Inhibitors
US8933024B2 (en) 2010-06-18 2015-01-13 Sanofi Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases
WO2012120058A1 (en) 2011-03-08 2012-09-13 Sanofi Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof
WO2012120056A1 (en) 2011-03-08 2012-09-13 Sanofi Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof
WO2012120051A1 (en) 2011-03-08 2012-09-13 Sanofi Benzyl-oxathiazine derivates substituted with adamantane or noradamantane, medicaments containing said compounds and use thereof
WO2012120050A1 (en) 2011-03-08 2012-09-13 Sanofi Novel substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof
WO2012120057A1 (en) 2011-03-08 2012-09-13 Sanofi Novel substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof
WO2012120053A1 (en) 2011-03-08 2012-09-13 Sanofi Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
WO2012120055A1 (en) 2011-03-08 2012-09-13 Sanofi Di- and tri-substituted oxathiazine derivates, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
US8901114B2 (en) 2011-03-08 2014-12-02 Sanofi Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof
US8828994B2 (en) 2011-03-08 2014-09-09 Sanofi Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof
JP2017531011A (en) * 2014-10-16 2017-10-19 ザ ボード オブ トラスティーズ オブ ザ リーランド スタンフォード ジュニア ユニバーシティ Novel methods, compounds and compositions for anesthesia

Family Cites Families (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US481088A (en) * 1892-08-16 Hydrocarbon-burner
US4348385A (en) * 1980-11-17 1982-09-07 Mobay Chemical Corporation Flowable pesticides
US4610868A (en) * 1984-03-20 1986-09-09 The Liposome Company, Inc. Lipid matrix carriers for use in drug delivery systems
US4826689A (en) * 1984-05-21 1989-05-02 University Of Rochester Method for making uniformly sized particles from water-insoluble organic compounds
FR2608988B1 (en) * 1986-12-31 1991-01-11 Centre Nat Rech Scient PROCESS FOR THE PREPARATION OF COLLOIDAL DISPERSIBLE SYSTEMS OF A SUBSTANCE, IN THE FORM OF NANOPARTICLES
EP0379591B1 (en) * 1988-06-28 1994-01-19 Matsushita Electric Industrial Co., Ltd. Exhaust smoke purifier apparatus
FR2651680B1 (en) * 1989-09-14 1991-12-27 Medgenix Group Sa NOVEL PROCESS FOR THE PREPARATION OF LIPID MICROPARTICLES.
CA2044706C (en) * 1990-06-15 2003-02-25 Michael Midler Jr. Crystallization method to improve crystal structure and size
US5145684A (en) * 1991-01-25 1992-09-08 Sterling Drug Inc. Surface modified drug nanoparticles
DK0615445T3 (en) * 1991-12-05 1996-06-03 Alfatec Pharma Gmbh Pharmaceutically manageable nanosol and method of preparation thereof
FR2692575B1 (en) * 1992-06-23 1995-06-30 Sanofi Elf NOVEL PYRAZOLE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
US5468604A (en) * 1992-11-18 1995-11-21 Eastman Kodak Company Photographic dispersion
GB9319129D0 (en) * 1993-09-15 1993-11-03 Dowelanco Ltd Storage and dilution of stable aqueous dispersions
SE9303281D0 (en) * 1993-10-07 1993-10-07 Astra Ab New formulation
SE9403846D0 (en) * 1994-11-09 1994-11-09 Univ Ohio State Res Found Small particle formation
DE4440337A1 (en) * 1994-11-11 1996-05-15 Dds Drug Delivery Services Ges Pharmaceutical nanosuspensions for drug application as systems with increased saturation solubility and dissolution rate
US5665331A (en) * 1995-01-10 1997-09-09 Nanosystems L.L.C. Co-microprecipitation of nanoparticulate pharmaceutical agents with crystal growth modifiers
US6074966A (en) * 1996-09-09 2000-06-13 Zlatkus; Frank P. Nonwoven fabric composite having multi-directional stretch properties utilizing a cellular or foam layer
DK0951280T3 (en) * 1996-10-03 2004-05-17 Hermes Biosciences Inc Hydrophilic microparticles and processes for their preparation
FR2758723B1 (en) * 1997-01-28 1999-04-23 Sanofi Sa USE OF CENTRAL CANNABINOID RECEPTOR ANTAGONISTS FOR THE PREPARATION OF DRUGS
US6127520A (en) * 1997-04-15 2000-10-03 Regents Of The University Of Michigan Compositions and methods for the inhibition of neurotransmitter uptake of synaptic vesicles
FR2766368B1 (en) * 1997-07-24 2000-03-31 Univ Claude Bernard Lyon METHOD FOR PREPARING NANOCAPSULES OF THE VESICULAR TYPE, USABLE IN PARTICULAR AS COLLOIDAL VECTORS OF PHARMACEUTICAL OR OTHER ACTIVE PRINCIPLES
US6375986B1 (en) * 2000-09-21 2002-04-23 Elan Pharma International Ltd. Solid dose nanoparticulate compositions comprising a synergistic combination of a polymeric surface stabilizer and dioctyl sodium sulfosuccinate
FR2789079B3 (en) * 1999-02-01 2001-03-02 Sanofi Synthelabo PYRAZOLECARBOXYLIC ACID DERIVATIVE, ITS PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME
US6383471B1 (en) * 1999-04-06 2002-05-07 Lipocine, Inc. Compositions and methods for improved delivery of ionizable hydrophobic therapeutic agents
US6372777B1 (en) * 1999-12-23 2002-04-16 Icos Corporation Cyclic AMP-specific phosphodiesterase inhibitors
CA2399791A1 (en) * 2000-02-11 2001-08-16 Bristol-Myers Squibb Company Cannabinoid receptor modulators, their processes of preparation, and use of cannabinoid receptor modulators in treating respiratory and non-respiratory diseases
ATE365537T1 (en) * 2001-08-06 2007-07-15 Astrazeneca Ab AQUEOUS DISPERSION OF STABLE NANOPARTICLES OF A WATER-INSOLUBLE ACTIVE SUBSTANCE AND AN EXCIPIENT SUCH AS MEDIUM-CHAIN TRIGLYCERIDES (MCT)
CA2461144A1 (en) * 2001-09-24 2003-04-03 Bayer Pharmaceuticals Corporation Preparation and use of pyrrole derivatives for treating obesity
US20060003012A9 (en) * 2001-09-26 2006-01-05 Sean Brynjelsen Preparation of submicron solid particle suspensions by sonication of multiphase systems
SE0104330D0 (en) * 2001-12-19 2001-12-19 Astrazeneca Ab Therapeutic agents
GB0216700D0 (en) * 2002-07-18 2002-08-28 Astrazeneca Ab Process
GB0302673D0 (en) * 2003-02-06 2003-03-12 Astrazeneca Ab Pharmaceutical formulations
GB0302672D0 (en) * 2003-02-06 2003-03-12 Astrazeneca Ab Pharmaceutical formulations
GB0302671D0 (en) * 2003-02-06 2003-03-12 Astrazeneca Ab Pharmaceutical formulations
US20060135523A1 (en) * 2003-06-18 2006-06-22 Astrazeneca Ab 2-substituted 5,6-diaryl-pyrazine derivatives as cb1 modulator
GB0314057D0 (en) * 2003-06-18 2003-07-23 Astrazeneca Ab Therapeutic agents

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